Sit on the Right side of the plane for the best views on flights from Chicago to Madrid. Right-side seats win overall due to the superior takeoff experience over Lake Michigan and Chicago's waterfront, which is more visually striking than the approach to Madrid. The landing views are comparable between sides, but the dramatic water and urban contrast at departure gives right a decisive advantage.

During takeoff from Chicago Midway International (MDW), sit on the Right side for the best views. Right-side seats offer views of Lake Michigan immediately after departure, with the Chicago shoreline and downtown skyline visible during climb-out. The aircraft typically departs eastbound or northeast, positioning right-side passengers for the clearest water and urban views. Notable sights include: Lake Michigan, Chicago downtown skyline, Indiana shoreline to the southeast, Calumet River industrial area.

When landing at Barajas (MAD), sit on the Left side for the best views. Left-side seats provide excellent views during approach to Madrid. The aircraft descends over the Spanish meseta (central plateau), and left-side passengers see the Sierra de Guadarrama mountains to the north and the sprawling Madrid metropolitan area. Approach typically comes from the northwest, making the left side optimal. Notable sights include: Sierra de Guadarrama mountain range, Madrid city sprawl, Tagus River valley, Spanish central plateau (meseta).

The flight from Chicago Midway International (MDW) to Barajas (MAD) takes Approximately 9 hours 15 minutes to 9 hours 45 minutes.

The flight crosses the Atlantic Ocean for roughly 5 hours. Notable features include: the eastern seaboard of the United States (visible during initial climb, including the Appalachian Mountains if departing northbound); the Atlantic coastline of Newfoundland and Nova Scotia (if visible during early oceanic phase); the mid-Atlantic with no significant landmarks; the Irish and British coastlines approaching Europe (western UK visible as the aircraft descends toward European airspace); and the Bay of Biscay between the UK and Spain. The approach into Madrid crosses the Pyrenees region (visible to the north) and the Spanish interior plateau before descent into central Spain.